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Hey Will, i have two Mission Workshop bags - expensivo, but good quality and last for ages.
I have the Monty (messenger type) and Fitzroy (backpack)
The Monty was used for commuting day in day out until Covid hit - never missed a beat.
I use the Fitzroy as a weekend bag, used it for commuting once but it was a bit big!
Ever thought of using panniers? I've got the Ortlieb Quick Rack on my commuter at the moment.
Well, that led to me purving out on this - https://missionworkshop.com/products/mission-workshop-x-carryology-control-collection
A $550 backpack